AI Trip Planner

Plan a trip with
credit card points

Pick origin + destination + month → see best award flights, top hotels bookable on points, attractions, signature events, and the cards whose welcome bonus would cover the trip. 41 US origin airports, no bank link required.

Boston, MA

US

Boston, MA

Freedom Trail, Harvard / MIT, Fenway Park, fall foliage walks

Pay in cash

$3,200

$200 flight + $3,000 hotel

Pay with points

187,000 pts

+ $30 taxes & fees

12KSouthwest175KHyatt

Best card for this trip

Chase World of Hyatt

60K bonus = 1.7 nights at XV Beacon + free night cert

Apply

Weather in June

☀️ Peak season — ideal time to visit

Air temp

62°–76°F

17°–24°C

Rainfall

low

Crowds

Peak

Warm, ideal weather

Switch month

Best months Shoulder Off-season

FlightsJFKBOS

Economy
  • Chase Ultimate Rewards

    via Southwest Rapid Rewards

    JFK → BOS — check direct flights from JFK. Chase UR → Southwest LGA-BOS

    8K/12K/18K

    roundtrip · Wanna Get Away (dynamic)

    + $30 taxes

  • JetBlue TrueBlue

    JFK → BOS — check direct flights from JFK. JetBlue (or Amtrak Acela alternative)

    12,000

    roundtrip

    + $20 taxes

Top hotels for your points

⭐ Top picks

Picked for best points value — Hyatt has the only fixed award chart left in major US hotels, so your points stretch the furthest here. Tap each option below for why it stands out.

  • XV Beacon

    Hyatt·Boutique luxury

    Cat 6 Unbound — Beacon Hill boutique.

    25K/30K/35K

    off / std / peak · Hyatt Cat 7

    $600/night cash

    5 nights = 175,000 pts (~$3,000 value)

  • Hyatt Regency Boston

    Hyatt·Central, transit

    Cat 4 — downtown near Boston Common.

    17K/20K/23K

    off / std / peak · Hyatt Cat 5

    $320/night cash

    5 nights = 100,000 pts (~$1,600 value)

  • Hyatt Centric Faneuil Hall Boston

    Hyatt·Historic walkable

    Cat 5 — boutique near Faneuil Hall + harbor.

    21K/25K/29K

    off / std / peak · Hyatt Cat 6

    $380/night cash

    5 nights = 125,000 pts (~$1,900 value)

  • Hyatt Place Boston / Downtown

    Hyatt·Budget, near Amtrak

    Cat 5 — South Station, includes breakfast.

    21K/25K/29K

    off / std / peak · Hyatt Cat 6

    $280/night cash

    5 nights = 125,000 pts (~$1,400 value)

Trip Strategy — open these cards and the trip is mostly free

Open Sapphire Preferred + World of Hyatt. XV Beacon (Hyatt Unbound Cat 6) — combined bonuses cover 4 nights + JetBlue/SW flight.

75K UR → 14K SW for RT + 2 nights at XV Beacon

$795/yr annual fee

60K bonus = 1.7 nights at XV Beacon + free night cert

$95/yr annual fee

Your out-of-pocket budget for this trip

Local transport$100
Food (5 days)$350
Activities (5 days)$275
Total cash needed$725

🚗 T subway + walking — best in New England · vs. $3,200 full cash trip

What to see & do in Boston, MA

  • Freedom Trail

    Sight

    2.5-mile red-brick line connecting 16 Revolutionary War sites. Self-guided or tour.

  • Harvard + MIT (Cambridge)

    Day trip

    Walk Harvard Yard; tour MIT campus + Stata Center. Red Line from downtown.

  • Fenway Park

    Sight

    Oldest MLB park (1912). Game, tour, or Green Monster seats. Iconic.

  • Faneuil Hall + Quincy Market

    Neighborhood

    1742 marketplace + food hall + cobblestones. Tourist hub, but classic.

  • North End

    Neighborhood

    Italian neighborhood with 100+ restaurants in 1 sq mile. Mike's Pastry or Modern.

  • Boston Public Garden + Common

    Sight

    America's first public botanical garden + Swan Boats (Apr-Sep).

Events to know about

  • Boston Marathon

    Patriot's Day (3rd Monday of April) — world's oldest annual marathon.

    Apr
  • 4th of July on the Esplanade

    Boston Pops concert + massive fireworks over Charles River.

    Jul
  • Head of the Charles Regatta

    Late October — world's largest 2-day rowing event.

    Oct
  • Saint Patrick's Day Parade

    South Boston — one of largest in the US.

    Mar